Manufacture of monoazo-dyestuffs



Patented Jan. 10, 1933 UNITED STATES PATENT OFFICE .51 OSCAR KNECHT AND THEODOR WIRTH, OF BASEL, SWITZERLAND, ASSIGNORS TO THE FIRM CHEMICAL WORKS FORMERLY SANDOZ, OF BASED, SWITZERLAND MANUFACTURE OF MONOAZO-DYESTUFFS No Drawing. Application filed May 10, 1929, Serial No. 362,148, and in Germany May 26, 1928.

been used for the manufacture of azo-dyestuffs. According to U. S. Patent No. 1,678,599 diazo compounds of amino-aryl sulphamides of the above mentioned constitution, in which the amino group stands in orthoor in meta-position to the sulphamlde group, are combined with 2.3-hydroxy-naphthoic acid arylides, whereby insoluble dyestufis are produced. In U. SQ Patents Nos. 1,429,781 and 1,429,782soluble azo-dyestuti's are described, obtainable by combining in acid solution with Q-amino-S-naphthol-G- sulphonic acid compounds or with 2-naphthylamine-S-sulphonic acids such diazotized 4-nitraniline sulphamides, in which the "2H sulphamide group is substituted in a similar manner by alkyl or aryl groups.

It has been found thatnew azo-dyestufls of excellent dyeing properties containing at least one halogen atom can be obtained by coupling diazotized l-aminobenzene-3-sulphamides of the general formula:

alkyl S O r-N phenyl wherein R stands for alkyl' or halogen, with a sulpho-1-phenyl-5-pyrazolonic compound of the general formula:

wherein X stands for GH or COOH and wherein one or'both of Y, Z stand for hydrogen or halogen.

, The new dyestufl's constitute in a dry state'yellow powders, easily soluble in water with a yellow coloration anddissolving in concentrated sulphuric acid with a yellow coloration. They dye wool from clear greenish yellow to yellow tints of excellent fastness to fulling, light and "perspiration. Contrary to this result, the corresponding dyestuffs derived from 4-nitraniline-2-sulphoalkylarylides show an insufficient fastness to fulling' and to perspiration, as their shade turns from'yellow to red.

In order to illustrate the invention the following examples are given, the parts being by weight:

Example 1 H N=N-( J0 HOOO (g=NNC SOIH The dyestufl? forms a yellow powder and dissolves in concentrated sulphuric acid with a brownish yellow and in water with a yellow coloration. It yields upon reduction 4-amino- 1 chloro -benZene-2 -sulphoethylanilide and 4-amino-4-sulpho-1-phenyl-3-carb0xyl- 5-,pyrazolone. It dyes wool clear yellow shades of good ,fastness to fulling, light and perspiration.

Emample 2 290 parts of the hitherto undescribed l-aminobenzen-e 4 methyl 3 sulphoethylanilide,

melting at 108 C. (obtained by the action of 1 nitrobenzene -4- methyl 3} sulphonic chlo ride upon monoethylaniline and subsequent reduction) are diazotized in the usual manner. The diazo solution thus obtained is added to a solution of 323 parts of ll-sulpho- 2 5 dichlor -1- phenyl -3-n1ethyl -5 -pyraz0- lone in water, containing an excess of sodium acetate. The resulting dyestufi' shows the formula:

02H: So -N oaHl H 01 I l wherein R stands for hydrogen, alkyl or halogen, with a sulpho-l-phenyl-5-pyrazolonic compound of the general formula:

zLd-soni wherein X stands for CH or COOH and wherein one or both of Y, Z stand for hydrogen or halogen.

2. A process for the manufacture of monoazo dyestuffs, consisting in coupling diazotiZed 1-aminobenzene-S-sulphamides of the general formula:

' alkyl SOr-N phenyl NHg wherein R stands for hydrogen, alkyl or halo gen, with halogenated l-sulphophenyl-B-pyrazolone compounds of the general formula:

wherein X stands for GH or COOH and wherein one or both of Y, Z stand for halogen.

3. A process for the manufacture of monoazo dyestuffs, consisting in coupling diazotized 1-aminobenzene-3-sulphamides of the general formula:

wherein R stands for hydrogen, alkyl or halogen, with 4;-sulpho-2 :5-dichloro-1-phenyl- 3-methyl-5-pyrazolone of the formula:

SIOaH 4:. As new products, the monoazo dyestuffs, containing at least one halogen atom and corresponding to the following general formula:

wherein R stands for hydrogen alkyl or halogen, and X for CH or COH, and wherein one or both of Y, Z stand for hydrogen or halogen, said dyestuffs constituting in the form of their sodium salts yellow powders, dissolving in water with a yellow coloration and in concentrated sulphuric acid with a brownish coloration, dyeing wool greenishyellow to yellow tints of excellent fastness to light, perspiration and fulling and yielding upon reduction l-aminobenzene-3-sulphamides and 4:-amino-l-sulphophenyl-5-pyrazolones.

5. As new products, the monoazo dyestuffs of the following general formula:

SOsH

wherein R stands for hydrogen, alkyl or halogen, and X for CH or COOH, and wherein one or both of Y, Z stand for halogen, said dyestuffs constituting in the form of their sodium salts yellow powders, dissolving in water with a yellow coloration and in concentrated sulphuric acid with a brownish yellow coloration, dyeing wool greenish yellow tints of excellent fastness to light, perspiration and fulling and yielding upon reduction 1-aminobenzene-3-sulphamides and halogenated l-amino-l-sulphophenyl-3-methyl (or carboxyl) -5-pyrazolones.

6. As new products, the monoazo dyestufi's of the following general formula:

0 R 00 S Or-N phony] 0 01 35 N=N-l-O wherein R stands for hydrogen, alkyl and halogen, said dyestuffs constituting in the form of their sodium salts yellow powders dissolving in water with a yellow and in concentrated sulphuric acid with a brownish yellow coloration, dyeing wool greenish yellow tints of excellent fastness to light, perspiration and fulling and yielding upon reduction 1-aminobenzene-3-sulphamides and 4-amino -l-sulpho-2' 5-d-ichloro-1-phenyl- 3-methylpyrazolone.

In witness whereof we have hereunto signed our names this 30th day of April 1929.

OSCAR KNEGHT. THEODOR WIRTH. 

